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So the bottom line is: I did my due diligence and filed the opt-out forms online, mailed the proof of coverage, contacted the lady at the student association who misinformed me and because ihaveaplan didn't receive the proof of coverage because of postage issues or breakdown at their office I am resonsible for paying the price!!

The ideas here for resolution are good, but I just want to state that after reading your post, in this world, you actually are in the wrong (well not necessarily wrong, read on). You can't prove that you mailed the document (i.e. it wasn't sent registered mail) and therefore don't have much ground to stand on.

Example: My GF and I ended up paying $1k in legal fees when the CRA "could not locate" the income tax return she mailed, which prevented her from getting her NOA, which was required to advance funds on the mortgage. Because she didn't send the envelope registered, we really can't prove that it was sent in the first place. Her not spending $8-10 in April cost us $1k in legal fees in July because we had to push the house closing back by 3 weeks while the CRA processed the re-sent tax return.

Lesson? Mail everything important registered, and take copies before you send it out.